Patent GB-998869-A (GB)
Title: Imido compounds, their production and use
IPC: C10M133/56
Filed: 1963-05-06
Abstract: A process for the production of an imide, bisimide or amic acid comprises reacting succinic anhydride, alkylsuccinic anhydride or alkenylsuccinic anhydride with a basic salt (or the corresponding base) of guanidine, aminoguanidine, guanylurea or biguanide or with urea, semicarbazide, 1,3-diaminourea or diaminoguanidine. The basic salt is preferably a carbonate, a bicarbonate or an aliphatic acid salt (e.g. an acetate).  Reaction is suitably at 75 DEG  to 175 DEG C. in a hydrocarbon solvent or in an oil medium.  Example 6 describes the preparation of N-amidinosuccinamic acid from succinic anhydride and guanidine carbonate at 110 DEG  to 112 DEG  C.  Example 7 describes the preparation of N - amidinotetrapropenyl - succinamic acid from tetrapropenyl succinic anhydride and guanidine carbonate at 85 DEG  C.  Example 14 describes the preparation of N,N1-bis(tetrapropenyl succinimide) methyleneimine from tetrapropenyl succinic anhydride and guanidine carbonate at 130 DEG  to 135 DEG C.ALSO:Polyalkenyl succinimides of formulae <FORM:0998869/C3/1> wherein R is polyalkenyl, m is 0 or 1, n is 0 or 1, R is H or <FORM:0998869/C3/2> and X is O or =NH are obtained by reacting equimolar amounts of (i) an alkenyl succinic anhydride or formula <FORM:0998869/C3/3> wherein R is polyalkenyl, with (ii) a basic salt of guanidine, aminoguanidine, guanylurea or biguinidine. Bis-polyalkenyl succinimides of formulae <FORM:0998869/C3/4> wherein R is polyalkenyl, m is 0 or 1, n is 0 or 1, y is 0 or 1 and X is 0 or =NH are obtained by reacting about 2 mols. of (i) with 1 mol. of (ii). The basic salt may be a carbonate, bicarbonate, or an aliphatic acid salt, e.g. an acetate. In a modification of the above process the basic salts may be replaced by the corresponding base or by urea, semicarbazide, 1,3-diaminourea or diaminoguanidine. The preferred polyalkenyl succinic anhydride derivatives are N-carbamoyl-, N-amidino-, N-ureido-, N-guanidino-, N - (N - carbamoylamidino)-, and N - (N - guanylamidino) - polybutenyl succinimides, bis - (polybutenylsuccinimido) methylene - imines, 1,N - bis - (polybutenylsuccinimido) formamides and formamidines, 1,3-bis-(polybutenylsuccinimido) ureas and guanidines, and N - [N - polybutenylsuccinimido (guanyl-methyleneimino or carbamoylaminido)] polybutenylsuccinimides. The products find application as detergent additives in lubricating oils, fuel oils and gasoline.ALSO:The invention comprises detergent additives for oils and fuels, viz. polyalkenyl succinimides of formulae <FORM:0998869/C4-C5/1> wherein R is polyalkenyl, m is 0 or 1, n is 0 or 1, R is H or -C-NH2 and X is 0 or = NH and X obtained by reacting equimolar amounts of (i) an alkenyl succinic anhydride of formula <FORM:0998869/C4-C5/2> wherein R is polyalkenyl, with (ii) a basic salt of guanidine, aminoguanidine, guanylurea or biguinidine; and bis-polyalkenyl succinimides of formulae <FORM:0998869/C4-C5/3> wherein R is polyalkenyl, m is 0 or 1, n is 0 or 1, y is 0 or 1 and X is 0 or = NH and obtained by reacting about 2 mols. of (i) with 1 mol. of (ii). The basic salt may be a carbonate, bicarbonate, or an aliphatic acid salt, e.g. an acetate. In a modification of the above process the basic salts may be replaced by the corresponding base or by urea, semicarbazide, 1,3-diaminourea or diaminoguanidine. The preferred polyalkenyl succinic anhydride derivatives are N-carbamoyl-, N-amidino-, N-ureido-, N-guanidino-, N - (N - carbamoylamidino)-, and N - (N - guanylamidino) - polybutenyl succinimides, bis - (polybutenylsuccinimido) methyleneimines, 1,N - bis - (polybutenylsuccinimido) formamides and formamidines, 1,3-bis-(polybutenylsuccinimido) ureas and guanidines, and N-[N-polybutenylsuccinimido (guanyl-methylene-imino or carbamoylaminido)] polybutenylsuccinimides. The products find application as detergent additives in lubricating oils, fuel oils and gasoline. Conventional additives also may be present, in particular metal phosphorodithioates or metal salts of phosphorus sulfideolefin polymer reaction products. Lubricating oil bases specified are hydrocarbon oils, alkylene polymers, alkylene oxide polymers, olefinchlorinated hydrocarbon polymers, dicarboxylic acid esters, alkylated benzenes, silicate esters and silicon polymers.